Total synthesis, revised structure, and biological evaluation of biyouyanagin A and analogues thereof.
Total synthesis, revised structure, and biological evaluation of biyouyanagin A and analogues thereof.
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DOI：
10.1021/ja802805c
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发表时间：
2008-08-20
影响因子：
15
通讯作者：
Burton, Dennis R.
中科院分区：
文献类型：
--
作者：
Nicolaou, K. C.;Wu, T. Robert;Sarlah, David;Shaw, David M.;Rowcliffe, Eric;Burton, Dennis R.
分离自金丝桃属植物H.中国湖变种根据NMR波谱分析，将其结构归属为1a或1b。这种新的天然产物表现出显着的抗HIV特性和抑制脂多糖诱导的细胞因子的产生。本文介绍了吡优烟配基A和几个类似物（3-11）的全合成、吡优烟配基A到2b的结构修正以及所有合成化合物的生物学性质。全合成通过级联序列进行，有效地产生对映体纯或富集的关键结构单元15 b（ent-zingiberene）和18（hyperolactone C），并具有新颖的[2+2]光诱导环加成反应，该反应具有完全的区域和立体选择性。用合成的biyouyanagin A（2-11）和hyperolactone C（12-16）进行的生物学研究表明，biyouyanagin A的活性最可能存在于其hyperolactone C结构域。
Isolated from Hypericum species H. chinese L. var. salicifolium, biyouyanagin A was assigned structure 1a or 1b on the basis of NMR spectroscopic anaylsis. This novel natural product exhibited significant anti-HIV properties and inhibition of lipopolysaccharide-induced cytokine production. Described herein are the total syntheses of biyouyanagin A and several analogs (3-11), structural revision of biyouyanagin A to 2b, and the biological properties of all synthesized compounds. The total synthesis proceeded through cascade sequences that efficiently produced enantiomerically pure or enriched key building blocks 15b (ent-zingiberene) and 18 (hyperolactone C), and featured a novel [2+2] photoinduced cycloaddition reaction which occurred with complete regio- and stereoselectivity. Biological investigations with the synthesized biyouyangagins A (2-11) and hyperolactones C (12-16) revealed that the activity of biyouyanagin A most likely resides in its hyperolactone C structural domain.
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DOI：
10.1039/p19870000851
发表时间：
1987-04-01
期刊：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
影响因子：
--
作者：
BUTTRUS, NH;CORNFORTH, J;STUART, AS
通讯作者：
STUART, AS
影响因子：
3.6
作者：
CANTRELL, TS
通讯作者：
CANTRELL, TS
影响因子：
4.9
作者：
Ichinari, D;Ueki, T;Kinoshita, T
通讯作者：
Kinoshita, T
影响因子：
5.1
作者：
Kraus, GA;Wei, JQ
通讯作者：
Wei, JQ
影响因子：
16.6
作者：
Nicolaou, K. C.;Sarlah, David;Shaw, David M.
通讯作者：
Shaw, David M.